Luxury homes for sale & real estate in Sherman, CT

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ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Escape the city and discover this wonderful estate, formerly Brinsmade Farm, in Sherman, Connecticut, offered for the first time in 60 years. Set on approximately 10 scenic acres in the heart of charming Sherman, this exceptional country home combines timeless New England charm with modern living. Originally a working dairy farm, the property was transformed in 1945 when the barn became a private residence. The estate includes three dwellings, perfect for extended family, guests, or multi-generational living-the Main House, Carriage House, and Pool House-offering approximately 5,200 sq ft with 6 bedrooms and 5 full baths. The Main House showcases cathedral ceilings, exposed beams, wide-plan

$1,849,000

6 beds5 baths5,500 sq ft

6 Brinsmade Ln, Sherman, CT 06784

12 acre lot • 6 garage spots • Pool

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Sherman, NY:
Discover the rare opportunity to build your custom modern ranch in the tranquil countryside of Sherman, Connecticut, just minutes from the New York line. Nestled on a private, wooded 1.02-acre lot in the exclusive Timber Trails area, this to-be-built contemporary home blends sleek design with serene living. Built by renowned SHERMAN BUILDING DESIGNS, every element will reflect the latest in energy efficiency, smart-home technology, and clean architectural lines. Enjoy open-concept living with soaring ceilings, designer finishes, and seamless indoor-outdoor flow. The 2,240 sq ft layout is thoughtfully crafted for modern lifestyles, offering flexibility for remote work, entertaining, and mult

$1,250,000

3 beds2 baths2,240 sq ft

2 Coburn Road W, Sherman Coburn Rd W, Sherman, NY 06784

Private wooded lot • Energy efficiency • Open-concept living

Listing by Coldwell Banker Realty

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes i

$1,600,000

6 beds5.5 baths4,258 sq ft

201 Route 37 S, Sherman, CT 06784

Hidden nooks • Reimagined kitchen • Dual staircases

OPEN SUN, 11AM TO 2PM

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Grand FULLY FURNISHED 6,700 SF Mediterranean, direct waterfront on two seriously private acres in Sail Harbor Club. Entertainer's paradise offers unlimited possibilities. Dramatic NEW 26x13 Sun Room displays exciting wall of glass that overlooks NEW 36x14 porcelain tiled deck above sprawling NEW 39x21 covered porcelain tiled patio. NEW 90' deck surrounds 45' saltwater gunite pool having its own path for golf cart transport. Most desirable quiet end of Candlewood Lake advantageous to make unencumbered use of any kind of boat, water or jet ski. Soak in your privacy assured by towering cover of vintage trees, with serene views of undeveloped Deer Island. "Turn-Key" opportunity to imm

$3,795,000

4 beds5 baths6,704 sq ft

5 Sail Harbour Dr, Sherman, CT 06784

Two private acres • New sun room • Direct waterfront

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
This elegant four-bedroom home, built in 2021, is perfectly sited on 1.8 acres of professionally landscaped, private grounds. Designed for effortless single-level living, it features an open-concept layout with a chef's kitchen and center island, a welcoming living room with fireplace, and a sunlit dining area that all flows seamlessly to a covered porch with views toward the Housatonic River. The luxurious primary suite includes a spa-like bath with a soaking tub and an expansive walk-in closet. This level also offers an additional en-suite bedroom, along with two more bedrooms - one currently used as a media room - that share a stylish, contemporary jack-and-jill bathroom. For those seeki

$1,395,000

4 beds3.5 baths3,247 sq ft

73 Long River Rd, Sherman, CT 06784

Covered porch • Spa-like bath • Chef's kitchen

Property at 5 Stone Wall Ln, Sherman, CT 06784, 4 beds, 4.5 baths

$1,999,000

4 beds4.5 baths5,427 sq ft

5 Stone Wall Ln, Sherman, CT 06784

Property at 21 Holiday Point Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,199,000

4 beds3.5 baths4,854 sq ft

21 Holiday Point Rd, Sherman, CT 06784

Property at 42 Long River Rd, Sherman, CT 06784, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths3,350 sq ft

42 Long River Rd, Sherman, CT 06784

Property at 60 Long River Rd, Sherman, CT 06784, 4 beds, 4.5 baths

$1,195,000

4 beds4.5 baths3,675 sq ft

60 Long River Rd, Sherman, CT 06784

Property at 86 Route 37 Rd S, Sherman, CT 06784, 4 beds, 2.5 baths

$899,000

4 beds2.5 baths2,900 sq ft

86 Route 37 Rd S, Sherman, CT 06784

Property at 00 Anderson Rd, Sherman, CT 06784

$1,495,000

— beds— baths— sq ft

00 Anderson Rd, Sherman, CT 06784

Property at Rte 39 South, State Rte, Sherman, CT 06784

$850,000

— beds— baths— sq ft

Rte 39 South, State Rte, Sherman, CT 06784

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NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
This beautiful home on 2.6 private acres in New Milford, Connecticut is currently being built and ready for you to add your final touches. A thoughtfully designed living space, this home perfectly blends luxury, functionality, and style. The first floor features a spacious open layout with a modern eat-in kitchen, large island, and sliders leading to the deck where you can enjoy views of Candlewood Lake. A flexible first-floor room with a full bathroom provides the option for a guest suite or home office. Upstairs, you'll find four spacious bedrooms, including a primary suite with a walk-in closet and spa-like bath featuring a soaking tub and double sinks. Hardwood floors run throughout, an

$995,000

4 beds3.5 baths4,510 sq ft

10 Juniper Dr, New Milford, CT 06776

Private acres • Boat dock • Deeded beach rights

ABOUT THIS HOME
Luxury Home for sale in Sherman, NY:
A Bucolic Retreat in Prestigious Quaker Hill, nestled among grand equestrian estates in the coveted Quaker Hill community of Pawling, this magnificent country retreat artfully blends modern luxury with rustic charm. Set on five serene acres surrounded by rolling meadows, scenic horse farms, and distinguished country homes, 43 Meeting House Lane offers an inspiring escape that celebrates the best of Hudson Valley living. The property features a fully renovated three-bedroom main residence and a charming two-bedroom guest cottage, each with its own utilities—ideal for hosting guests, accommodating extended family, or providing a caretaker’s residence. Originally conceived as a cla

$1,995,000

5 beds4.5 baths5,390 sq ft

43 Meeting House Rd, Pawling, NY 12564

Five serene acres • Vaulted ceilings • 5 acre lot

Listing by Christie's Int. Real Estate

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Welcome to 23 and 24 Echo Drive, New Milford, CT-a timeless gem first introduced to the market by the family who originally built it. Nestled on the shores of Candlewood Lake within the prestigious Birch Groves community, this exquisite residence embodies the classic Adirondack style of the 1930s with its captivating stone and wood construction. Spanning 2,073 square feet, this elegant lake home offers four spacious bedrooms, a three season porch and a storybook living room with an impressive floor to ceiling field stone fireplace, providing ample space for relaxation and entertainment. With western exposure, enjoy breathtaking sunset views from the comfort of your home that seamlessly blen

$3,900,000

4 beds2.5 baths2,073 sq ft

23 Echo Dr, New Milford, CT 06776

0.63 acre lot • Built 1939 • Listed 28 days

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Stunning Renovated Colonial Retreat with Heated Pool & Cabana! Welcome to 3 Alexandra Drive, a beautifully renovated white Colonial tucked away on a private lot in one of New Fairfield's most desirable neighborhoods. This home perfectly blends classic charm with modern luxury, offering all the amenities you've been dreaming of! Step inside to a bright, inviting interior featuring a sophisticated color palette and thoughtful updates throughout. The renovated kitchen boasts stainless steel appliances, a center island with seating, and opens seamlessly to the family room with a cozy gas fireplace and an 8' slider leading to the expansive back deck-ideal for indoor-outdoor living. The din

$925,000

3 beds2.5 baths2,704 sq ft

3 Alexandra Dr, New Fairfield, CT 06812

Custom dry bar • Outdoor sauna • Spa-like bathroom

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
This three-bedroom (possibly four bedroom), three-bathroom home sits on approximately 6.6 acres of land (originally three building lots). The home offers approximately 3,334 square feet of living space. The primary bedroom features an en-suite bathroom and provides ample space for a seating area or home office. The two additional bedrooms are well-proportioned and have access to the hallway bathroom. The kitchen is outfitted with stainless steel appliances, providing a modern and efficient cooking experience. The open floor plan allows the kitchen to flow seamlessly into the living and dining areas, creating a warm and inviting atmosphere for entertaining or casual gatherings. Outside, the

$875,000

3 beds3 baths3,334 sq ft

31 Cedar Hill Rd, Gaylordsville, CT 06755

Open floor plan • Hot tub • Barn studio

ABOUT THIS HOME
Luxury Home for sale in Sherman, CT:
Don't miss this newly listed one of a kind home nestled on 8.44 private acres with views so outstanding they could take your breath away. This 5700 plus sq. ft. home w/ 6 generous sized Brs, 5.5 baths is only the start. Its primary Br. 25X18 w/ Fp, Lg. tiled bath w/ jacuzzi & those mountain top views again then to a spacious walk/in closet. There are an additional 4 more bedrooms all with oak floors on this level. ( 2nd Floor ) The main level all with oak floors. (exception tile foyer) features a lg. country equipped kitchen w/ all appliances, center island, granite counters, dinning area and more abutting 23' a family room a w/ 10 ft' ceiling & gas Fp. There is two car garag

$1,250,000

6 beds6.5 baths5,710 sq ft

5 Lyric Ln, New Milford, CT 06776

Private acres • Mountain top views • 8.44 acre lot

Property at 35 Skyline Dr, Sherman, CT 06784, 3 beds, 2.5 baths

$1,395,000

3 beds2.5 baths3,020 sq ft

35 Skyline Dr, Sherman, CT 06784

Property at 1 Pinecrest Ln, New Fairfield, CT 06812, 4 beds, 3.5 baths

$1,199,900

4 beds3.5 baths3,204 sq ft

1 Pinecrest Ln, New Fairfield, CT 06812

Property at 6 Pinewood Dr, New Fairfield, CT 06812, 4 beds, 3 baths

$859,500

4 beds3 baths3,858 sq ft

6 Pinewood Dr, New Fairfield, CT 06812

Property at 32 Sail Harbour Dr, New Fairfield, CT 06812, 4 beds, 5.5 baths

$1,495,000

4 beds5.5 baths6,052 sq ft

32 Sail Harbour Dr, New Fairfield, CT 06812

Property at 4 Harbour View Dr, New Fairfield, CT 06812, 4 beds, 3.5 baths

$3,195,000

4 beds3.5 baths3,688 sq ft

4 Harbour View Dr, New Fairfield, CT 06812

Property at 73 Lake Ellis Rd, Wingdale, NY 12594, 4 beds, 3 baths

$899,000

4 beds3 baths1,850 sq ft

73 Lake Ellis Rd, Wingdale, NY 12594

Listing by Keller Williams NY Realty

Property at 604 N Quaker Hill Rd, Pawling, NY 12564, 5 beds, 7.5 baths

$1,450,000

5 beds7.5 baths5,470 sq ft

604 N Quaker Hill Rd, Pawling, NY 12564

Listing by Ellis Sotheby's Intl Realty

Property at 57 Indian Trail Rd, New Milford, CT 06776, 4 beds, 4 baths

$6,200,000

4 beds4 baths6,236 sq ft

57 Indian Trail Rd, New Milford, CT 06776

Property at 430 Long Mountain Rd Lot 1, New Milford, CT 06776, 4 beds, 3.5 baths

$2,800,000

4 beds3.5 baths4,000 sq ft

430 Long Mountain Rd Lot 1, New Milford, CT 06776

Property at 427 Long Mountain Rd, New Milford, CT 06776, 4 beds, 4.5 baths

$964,900

4 beds4.5 baths4,848 sq ft

427 Long Mountain Rd, New Milford, CT 06776

Property at 155 Shortwoods Rd, New Fairfield, CT 06812, 4 beds, 5 baths

$1,199,000

4 beds5 baths5,036 sq ft

155 Shortwoods Rd, New Fairfield, CT 06812

Property at Candlewood Mountain Rd, New Milford, CT 06776

$2,200,000

— beds— baths— sq ft

Candlewood Mountain Rd, New Milford, CT 06776

$1,700,000

— beds— baths— sq ft

Candlewood Mountain Rd, New Milford, CT 06776

Property at Spooner Hill Rd, Kent, CT 06757

$895,000

— beds— baths— sq ft

Spooner Hill Rd, Kent, CT 06757

Based on information submitted to the MLS GRID as of Fri Dec 05 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Luxury Homes for Sale in Sherman

There are currently 12 luxury homes for sale in Sherman at a median listing price of $884K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Sherman stay on the market for 94 days and receive 1 offers. This map is refreshed with the newest listings in Sherman every 15 minutes.

In the past month, 4 homes have been sold in Sherman. In addition to houses in Sherman, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Sherman last month. Find your dream home in Sherman using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Sherman are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Sherman. If you're looking to sell your home in the Sherman area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Sherman with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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